Story related. Complete Chapter 1 to unlock.

Story related. Complete Chapter 2 to unlock.

You'll get this in the course of Chapter 2, once Joe takes you to meet Mike Bruski. Bring the Walter Coupe back to Mike and this trophy will pop. Fuhgeddaboudit!

Near the begninning of Chapter 2 you will spot your sister Francesca in an alley arguing with a thug. When you intervene he will start a fight with you (this will be the melee combat tutorial). Win the fight and you'll earn this trophy.

Near the beginning of Chapter 2 (after getting the Big Brother trophy), while walking to Joe's apartment you'll pass a man and woman fighting over a broken down car. From your starting point they'll be across the street in an alley next to the wooden fence. As you approach you'll hear them arguing. When they finish, the husband will leave. Fix the car to receive the trophy.

Video guide courtesy of PowerPyx.

Story related. Complete Chapter 3 to unlock.

In Chapter 3, you will have to infiltrate the Office of Price Administration, steal the gas ration stamps and escape without being detected. All guards must be subdued stealthily by creeping up behind them and pressing the button before attempting the theft. You will also need to disable the silent alarm in the basement before opening the safe, or reinforcements will appear outside during your escape. After you steal the stamps, go out through the Hearing Room on the second floor, the coal chute in the basement, or out the way you came in. If you were not seen, didn't fire your gun and did not set off the silent alarm, you'll get the trophy once you get over the gate at the end.

Video guide courtesy of PowerPyx.

At the end of chapter 3 you're on the hook to sell the 6 ration stamps before they expire at midnight. Once Henry gives the word, your countdown will begin and all gas stations will ne highlighted on your minimap. You can only sell one stamp at each gas station, and there are eight stations, so plan your route carefully. You will have to move quickly to make the deadline, but be careful not to attract any heat. When you get to a station, you won't have to get out of the car. Just pull up between the pumps and the office and stop, and you will get a prompt to sell the stamps with the button. Once Vito starts to talk with the attendant, set a waypoint for the next station in the sequence. Once the deal is done, head to the next station immediately. If you manage to sell all six before the time runs out, you'll get the trophy. Use the map below for a suggested route.

Story related. Complete Chapter 4 to unlock.

Story related. Complete Chapter 5 to unlock.

Story related. Complete Chapter 6 to unlock.

Story related. Complete Chapter 7 to unlock.

Story related. Complete Chapter 9 to unlock.

Story related. Complete Chapter 10 to unlock.

Story related. Complete Chapter 11 to unlock.

In Chapter 11 when you have to warn Leo before he is killed, you have the opportunity to escape with him if you're fast enough. As soon as the cinematic with Leo is finished, run to the hamper outside the bathroom and grab a sheet. A cinematic will play showing your escape and you will receive the trophy.

Story related. Complete Chapter 12 to unlock.

Story related. Complete Chapter 13 to unlock.

Story related. Complete Chapter 14 to unlock.

You'll get this trophy at the end of Chapter 15 for whacking Carlo Falcone in the Hillwood Observatory. This trophy will pop during the ending, just after any difficulty related trophies you may have earned.

Finish the story on Medium or Hard difficulty. This trophy will stack with the Tough Nut trophy if you play on Hard difficulty for your first playthrough. NOTE: If you start a game at a lower difficulty, then use chapter select to go back and play at a higher difficulty, this trophy may not unlock for you once you have completed the game. Instead of using chapter select, choose the "New Game" option to start again at Medium or Hard difficulty and play through the first chapter. Once you've completed Chapter 1, if you've done all the other chapters at that difficulty, this trophy will unlock.

Finish the story on Hard difficulty. You will also get the Made Man trophy if you play on Hard difficulty for your first playthrough. NOTE: If you start a game at a lower difficulty, then use chapter select to go back and play at a higher difficulty, this trophy may not unlock for you once you have completed the game. Instead of using chapter select, choose the "New Game" option to start again at Hard difficulty and play through the first chapter. Once you've completed Chapter 1, if you've done all the other chapters at that difficulty, this trophy will unlock.

The easiest way to do this is to head east across the Grand Upper Bridge, building up as much speed as you can. Once you reach the end of the bridge, angle slightly to the left to hit the downhill slope of the road across the street and you should have no trouble clearing the 20m in your first attempt. If you have trouble with this trophy you can wait until Chapter 8 when you get a Hot Rod, however you can easily accomplish this with the Jefferson Provincial that you steal in Chapter 2 if you travel the length of the bridge to pick up speed before hitting the drop.

Video guide courtesy of PowerPyx.

Just like Get Rich or Die Flyin', find a long stretch of relatively traffic free road, switch off your speed limiter and give 'er. If you haven't gotten this trophy before Chapter 11, the Ascot Bailey you get early in the chapter is a perfect car for this. The base model is good, but even better with a Super Charge tuning. Aside from the DLC vehicles, it's one of the fastest in the game. As for location, you can attempt this on the freeway but I found it easier on the Grand Upper Bridge. No turns, less traffic and easier to avoid the Driving AI's random sideswipes.

Not a difficult trophy, but a boring one. 50 miles in the same vehicle means that particular vehicle, not one of the same type. Make sure that you store the vehicle in the garage before you start so that you'll be able to leave the car in random places, and it will always be available from the garage. Don't let it get destroyed however, or you'll have to start over with a new vehicle. That means you'll have to maintain the car, fuel it when necessary, and keep it running until the trophy pops.

You'll be able to keep track of your progress using the "Show Legend" option in your garage. The "Distance Traveled" stat will save at checkpoints at at the end of each chapter. If you have not completed this trophy by the end of the story, bear in mind that using Chapter Select to go back will cause your "Distance Traveled" stat for that vehicle to reflect the value it had at the beginning of that chapter. You will have to complete whatever is left of the 50 miles from that point in the story.

In Chapter 2 you'll meet Mike Bruski, and unlock an easy way to earn money. Beside his office in the junkyard is a car crusher, a.k.a "Mike's Beast". Drive a car into the crusher, walk up the metal stairs to the control panel and pull the lever with the button to earn $400 quick cash. After five cars are recycled, this trophy will pop.

Starting in Chapter 7 you'll unlock the ability to sell cars to Derek at the docks, and for a lot more money than what Mike's wrecking will net you. Remember that Derek only wants high end cars. Any car that has a lock with four or five tumblers will usually do. To sell the cars, you'll find a cargo lift on the pier just to the southeast of Derek's office door, next to the ship the cars will be be loaded onto. Drive five suitable vehicles onto the cargo lift at the docks, and the trophy is yours. Note that you will not be able to sell to Derek in Chapter 14 & 15 so plan accordingly.

Cars that Derek will buy include (but not limited to):
Ascot Bailey
Berkley Kingfisher
ISW 508
Jefferson Provincial
Lassiter Series 75 Hollywood
Shubert Frigate
Smith 34 Hot Rod
Walker Rocket

A good location to find high end cars regularly is the small parking lot just east of the park, shown in the map below.

See the map below for a suggested route. Try not to go too fast, not only because you'll have more difficulty maintaining control/speed, but you'll also eat up road faster and therefore have to maneuver more. Even though you should avoid traveling at high speeds, I recommend that you don't use the speed limiter however in areas where there is a lot of traffic or where the speed limit drops to 40. The AI drivers have a tendency to sideswipe you randomly, and while using the speed limiter it's very easy to dip below 30 if you happen to clip one of them. To minimize this, you can honk your horn as you're coming up on them and they will usually move out of your way. On the highway you can use the speed limiter if you prefer, but the speed limit on the highway is significantly higher. Don't travel too fast or you will run out of road on the highway and have to brave the city blocks in the northwest area of the map. If you manage your speed manually you can adjust dynamically as the situation requires, and not need more than a full lap. Credit to Burfid for the horn tip.

This should be fairly easy to accomplish with a rifle or pistol, but it is necessary for the headshot to kill your target. You can miss in between shots, as long as your headshot kills are relatively quick (5 headshot kills within about 30 seconds or so). The easiest place to try this is right at the beginning of the game in Chapter 1. In the initial attack at the start of the chapter there are five soldiers to kill while the crowd disperses. There is a second opportunity later in the chapter on the balcony before entering the room with the MG42. In both cases you may have to restart the mission if one of the other soldiers steals your kill, but it's still manageable.

Make sure you don't have a weapon equipped and use the and buttons to pummel your enemies. Incidentally, civilians also count towards this trophy so you can start fights on the street to round out your total. Police will break up the fight if they're in the area however, so go on and fight them too! Credit to Guttsu-87 for suggesting the collateral damage.

To rob a store, equip a weapon and aim it at the cashier with the button. While keeping them covered, move over to the cash register until the prompt to press to rob it comes up. Move to your next target and repeat four more times within 5 minutes. Be careful though, some stores hire protection to guard the loot. Remember that you can't rob Harry's Army Surplus, Giuseppe's shop, the Maltese Falcon, Freddy's Pub, or the Mona Lisa.

Gun shop owners will always be armed, but the stores are always empty and with a shotgun you can usually get the drop on them and get out before any cops arrive. If you prefer a safer approach, you can use the button to just shove the cashier out of the way, grab the money and run. It's a melee attack technically, so it's still considered a robbery. You're less likely to attract police attention, and even if you do it won't immediately be an armed response. You can attempt this anywhere, but below is a suggested route starting at the East Side gun shop. Thanks to Burfid for the pacifist approach.

Earn that button, and send fifty of theirs to the morgue.

The key word here is "luxury". Head over to Vangel's and buy either version of the Tailored Suit to unlock this trophy. Note that Vangel's is accessible from the beginning of the game, well before it is added to your map automatically in Chapter 9. Just south of the park on the East Side, in the larger of the two blocks with entrances on both sides of the store. The icon will appear as soon as you are in the area.

At any body shop, purchase the Basic tuning upgrade.

The description of this trophy is misleading. Though there are three levels of tuning available for cars (Basic, Sports, and Super Charge) you only have to upgrade to Sports tuning to get this trophy. It becomes available in Chapter 7 and costs around $800-1000 depending on the car you're upgrading.

When you're at a four star wanted level, stay alive for ten minutes and you'll earn this trophy. An easy place to get this trophy is at the end of Chapter 4, after Joe takes the loot and leaves you in the alley. Pop your head out to draw the police's attention. Once they see you, you'll instantly jump to a four star wanted level. Run back down the alley and take cover behind the small corner on the west side of the alley. Four or five cops will run in, while one will remain behind the fence at the mouth of the alley shooting in. Kill all the cops that enter the alley, leaving the one outside shooting. Stay behind cover, popping out once in a while to maintain your wanted level. This is also important because I've found that if you stay too long in cover, the cop will sometimes try to take advantage of the lull in the firefight to close the distance. Pop out regularly to get his attention, and he should keep his distance. You can do ten minutes easily this way, with minimal risk. Credit to immikeulate for this strategy.

See Ladies' Man or Card Sharp.

You should get this trophy over the course of the game. Simply drive 30 different types of vehicle and the trophy will pop. There are a total of 38 cars available in the game, not including DLC cars that will also count towards this total. To make this easier on yourself, try to get half of them before the events of Chapter 6. In Chapter 7 and beyond new car models are introduced, and many of the earlier cars are either very rare or unavailable.

In total there are 50 Playboy magazines to pick up.

CHAPTER 2 - 2 Playboys
1. JOE'S APARTMENT - On the coffee table.
3. MIKE'S GARAGE - Across from Mike Bruski's office is a a three car garage, the door to the right will be unlocked. It will be on a metal shelf against the wall on the right.

CHAPTER 3 - 5 Playboys
18. DEREK'S OFFICE - Steve will drop this just outside the office door near the stairs.
4. MARIA'S APARTMENT BUILDING - Just inside the doorway to the building, you'll find this in the dark corner behind the door to the left, next to a shelf.
5. OFFICE OF PRICE ADMINISTRATION - In the Industrial Specialist's office, across the hall from the Director's office. Enter and turn right, it will be on the windowsill.
40. OFFICE OF PRICE ADMINISTRATION - First floor, on the security guard's desk in the main hall.
6. OFFICE OF PRICE ADMINISTRATION - In the basement, coming out of the room with the safe alarm switch, go left and enter the room on the left. You'll find it on the floor between the first and second rack on the left side of the room.

CHAPTER 4 - 4 Playboys
9. MALL - While following Joe up the first set of stairs away from the bookstore there will be a box of books in the corner, with the Playboy next to it on the floor.
2. MALL - Immediately after #9, go through the door and down towards the doors to find a Playboy in the shadows under the stairwell.
8. MALL - On the roof, in the small room just before you jump down to the fire escape. It will be on the floor next to a shelf on the right.
7. JOE'S APARTMENT - At the end of the chapter, go down to the dark area with the locked gate to the basement and you'll find the Playboy next to the gate.

CHAPTER 5 - 3 Playboys
11. APARTMENT 233 - After using the MG42, go up the stairs instead of down and find a Playboy at the top, just around the corner.
10. DISTILLERY - First floor office across from the stairwell, on a shelf on the right side as you enter the room.
12. DISTILLERY - Fifth floor across from where you catch up with "The Fat Man", between two chain link cages on the floor near some chairs.

CHAPTER 6 - 3 Playboys
13. HARTMANN PENITENTIARY - From where you start in the yard, go due west and look around the corner to the right. You'll find the Playboy by a prisoner sleeping behind the bleachers.
14. HARTMANN PENITENTIARY - From where you start in the yard, go south and around the back of the gray shed by the basketball court.
15. HARTMANN PENITENTIARY - In the laundry room. Find this Playboy on top of one of the dryers after you fight.

CHAPTER 7 - 4 Playboys
16. HARRY's ARMY SURPLUS - On the floor near the stairs.
50. JOE'S APARTMENT - Before Joe takes you to your new apartment, go to the top floor of his building and find it on the hallway floor.
17. VITO'S APARTMENT - In the second floor hallway, on a side table.
46. VITO'S APARTMENT - On the kitchen table.
NOTE: For some people (including myself), Playboy #46 will not appear on the kitchen table in this chapter, especially if you open the door before your landlord does. If this Playboy doesn't appear in this chapter, it will appear either at the beginning of Chapter 8 or the end when you return to your apartment.

CHAPTER 8 - 3 Playboys
19. OLD FOUNDRY - After entering the foundry, go west all the way to the back of the area. Just as you turn the first corner, you'll see a shack to your left. The Playboy will be inside the shack on top of an oil drum.
21. OLD FOUNDRY - Loop around and come all the way back to the east side of the area. When you turn south, there will be a catwalk with a guy shooting at you with a Thompson. The Playboy will be on the ground just before the catwalk next to some oil drums
20. OLD FOUNDRY - When Joe suggests that you steal the hot rods, turn left and you'll see a set of stairs next to the last building. Go under the stairs and around the building to the right. Near the fire, you'll find the Playboy under a dirty cot.


CHAPTER 9 - 4 Playboys
41. MALTESE FALCON - On the bar.
23. SEWER - While in the sewer on the way to the slaughterhouse, take the right fork as you enter, then you will find the Playboy in the fork to the left just before the tunnel with the ladder out.
22. SLAUGHTERHOUSE - In the first room you enter on the left hand side near a metal bin.
24. SLAUGHTERHOUSE - In the far northeast corner of the room with the meat counters and butchers.

CHAPTER 10 - 4 Playboys
25. EMPIRE ARMS HOTEL - In the laundry area, find the "Daily Room." The Playboy is on the corner of the desk.
27. EMPIRE ARMS HOTEL - After cleaning the floor in the conference room, Joe opens the stairwell door. Go down to the 16th floor and the Playboy will be next to the security gate.
26. EMPIRE ARMS HOTEL - On the roof, on the same platform as the motor for the window cleaners lift.
48. VITO'S APARTMENT - At the end of the chapter, it will be in the larger bathroom attached to the bedroom. You'll find it just to the left of the door in the corner by the tub.

CHAPTER 11 - 5 Playboys
47. LEO GALANTE's HOUSE - 2nd floor on windowsill overlooking the front of the house.
29. LEO GALANTE's HOUSE - 2nd floor bathroom on the basket next to the sink.
28. ERIC'S FRIEND'S APARTMENT - Bedroom across from the entrance, next to a guy slumped against the closet.
49. JOE'S APARTMENT - On the floor next to Joe's bed.
30. HILL OF TARA PUB - Dead end hallway beside the bar, under a box at the end.

CHAPTER 12 - 3 Playboys
31. SEA GIFT WAREHOUSE - North of where you meet the Chinese contact at the end of the alley, on the ground behind an overgrown dumpster.
32. SEA GIFT WAREHOUSE - Southwest of where you meet the Chinese contact, on the ground between a truck and the loading dock.
33. SEA GIFT WAREHOUSE - After the cinematic, you'll climb the stairs and go across the walkway. Turn left, and it will be halfway down the hallway on the right, on the ground next to a junction box.

CHAPTER 13 - 3 Playboys
34. RED DRAGON RESTAURANT - In the southwest corner of the 2nd level of the dining area, above the bar. The Playboy will be on the seat of the corner booth.
36. RED DRAGON RESTAURANT - When you enter the opium den area, and come down the stairs, enter the lit shanty immediately to the left and you will find the Playboy just inside the door on the left.
35. RED DRAGON RESTAURANT - In the basement, on a box in the armory.

CHAPTER 14 - 3 Playboys
44. VINCI'S BUILDING - After escaping and dealing with all three of the heavies on that floor, head to the southeast and look for a palette of cement bags. Go down the little path to the right of the bags, and you'll find the Playboy just around the corner.
37. VINCI'S BUILDING - Third floor at the base of the stairs, on some palettes around the corner to the left.
38. VINCI'S BUILDING - After getting Playboy #37, climb up and over the platform and kill everyone in the hallway. Cross the hallway, go through the open door to the left and go south. You'll find the Playboy next to the back wall.

CHAPTER 15 - 4 Playboys
45. HILLWOOD OBSERVATORY - First floor, at the bottom of the stairwell. You can knock down the
barrier that "blocks" you from going down a floor. You'll find it in the corner next to the stairs.
39. HILLWOOD OBSERVATORY - Rooftop, on your way to the telescope dome turn right and go around
the edge of the building. It will be in a corner near the front of the building.
43. HILLWOOD OBSERVATORY - Behind the telescope, in a corner next to the stairs.
42. HILLWOOD OBSERVATORY - In the well next to the projector in the planetarium.

Collect all 159 Wanted Posters. Click below for numbered maps to all the posters. See the guide located in the forum for a detailed list of how to find each Wanted poster number.

Near the beginning of Chapter 3, Derek gives you a shot to prove yourself by collecting the "fee for the barber" from the dock workers in the warehouse. After collecting from three workers, a worker named Bill challenges you to a fight. Knock him out, bring the loot to Derek and you'll have the trophy.

Right at the beginning of Chapter 5, upon leaving the apartment you'll you'll see a car accident between Joe's "girlfriend" and an angry man. Fight the man and knock him out to receive the trophy.

At the end of Chapter 10, you'll receive a call to pick Joe up at the Lone Star bar. Shortly after arriving, he will accidentally kill the bartender. Drag Leon's body out to his car and stuff him in the trunk. Drive Joe back to his place, making sure to take your time since the cops will be very alert. Even passing a cop can net you a two star wanted level, so easy does it. After you drive Joe home, take a ride out to Mike's junkyard and crush the evidence.

In Chapter 11 your house will be burned down. Run away from your attackers and steal a car as soon as you can. Drive to Joe's and recruit him to attack the Hill of Tara pub. After you kill all the people inside, pick up the Grease gun that was dropped by the enemy near the back door. Equip this, then exit the back door to see the Irish leader try to flee in his car. Fire at either him or his gas tank to kill him quickly before he pulls away. If you fail to kill him, you'll have to chase him in Joe's car to finish the job.

In Chapter 14 you'll receive a mission to kill a witness as a favor for another family. After you eliminate the witness, you will be attacked by two cars worth of Federal Agents and receive a three star wanted level. Deal with the police however you prefer, then drive Joe to his car in Kingston to receive the trophy.

In Chapter 14 you'll get into a firefight with Steve and eventually Derek. This is probably the most difficult mission in the game, mostly because of the poor waypoint placement. Make your way down the pier, killing Steve and the other enemies on the way by. Eventually you'll make it to the warehouse for your fight with Derek.

METHOD 1: The easiest way I've found to do this is to immediately run for the far left side of the warehouse, under the platform Derek is on, killing the worker in front of you on the way or from the cover of one of the metal pillars. There will be another goon on the east side in the back, kill him too. Come back towards the front of the warehouse, stopping at the center pillar where you can hide behind a stack of boxes and a large cask. Edge left around the boxes slightly past the pillar to trigger two guys to run across the catwalk on the west side towards the stairs. Don't move out too far or the jamook on the platform above you will dome you almost instantly. Kill the two thugs before they reach the ground, then repeat the process until a second set of guys spawn.

Now you're ready to make your move. Move to the edge of the platform on the west side of the warehouse, turn around and look up. Using the pink circle that indicates Derek's location as a guide, lob a grenade or two straight up onto the platform using the circle on the minimap as a guide. One grenade should do the trick, two at most. Once Derek is dead, kill any of his men left in the warehouse and the trophy will pop.

METHOD 2: It turns out there's an even easier way to do this. Start off the same as Method 1 and kill off Steve and all the goons outside the warehouse. Then, before entering the warehouse get in your car and drive off the pier. Instead of killing you, the game respawns you on the pier. What's even stranger is that the warehouse door closes and you can gain entry via Derek's office. You can't be hit by molotovs while in there and you pretty much have a clear shot at everyone in relative safety. They'll probably fix this in a patch, but for now the method is almost foolproof.